7642-31-1Relevant academic research and scientific papers
Catalytic Cyclotrimerization Pathway for Synthesis of Selaginpulvilins C and D: Scope and Limitations
Rycek, Lukas,Mateus, Miguel,Beytlerová, Nela,Kotora, Martin
, p. 4511 - 4515 (2021/04/12)
A facile and unified approach to the main selaginpulvilin's framework was achieved by catalytic [2 + 2 + 2]-cyclotrimerization of a triyne with monosubtituted alkynes. The reaction proceeded with high "ortho"selectivity by using Wilkinson's catalyst (RhCl
Transition-Metal-Free Synthesis of Borylated Thiophenes via Formal Thioboration
Bel Abed, Hassen,Blum, Suzanne A.
supporting information, p. 6673 - 6677 (2018/10/24)
A simple, regiocontrolled, and transition-metal-free approach to access exclusively 3-borylated thiophene derivatives is reported. The commercially available B-chlorocatecholborane reagent (ClBcat) acts as a carbophilic Lewis acid to activate the alkyne i
Cyclobutene vs 1,3-Diene Formation in the Gold-Catalyzed Reaction of Alkynes with Alkenes: The Complete Mechanistic Picture
De Orbe, M. Elena,Amenós, Laura,Kirillova, Mariia S.,Wang, Yahui,López-Carrillo, Verónica,Maseras, Feliu,Echavarren, Antonio M.
supporting information, p. 10302 - 10311 (2017/08/09)
The intermolecular gold(I)-catalyzed reaction between arylalkynes and alkenes leads to cyclobutenes by a [2 + 2] cycloaddition, which takes place stepwise, first by formation of cyclopropyl gold(I) carbenes, followed by a ring expansion. However, 1,3-butadienes are also formed in the case of ortho-substituted arylalkynes by a metathesis-type process. The corresponding reaction of alkenes with aryl-1,3-butadiynes, ethynylogous to arylalkynes, leads exclusively to cyclobutenes. A comprehensive mechanism for the gold(I)-catalyzed reaction of alkynes with alkenes is proposed on the basis of density functional theory calculations, which shows that the two pathways leading to cyclobutenes or dienes are very close in energy. The key intermediates are cyclopropyl gold(I) carbenes, which have been independently generated by retro-Buchner reaction from stereodefined 1a,7b-dihydro-1H-cyclopropa[a]naphthalenes.
Total Synthesis of Selaginpulvilin C and D Relying on in Situ Formation of Arynes and Their Hydrogenation
Karmakar, Rajdip,Lee, Daesung
supporting information, p. 6105 - 6107 (2016/12/09)
The total syntheses of selaginpulvilins C and D is described. The key strategy for the construction of the core fluorene moiety involves in situ formation of an aryne intermediate followed by its formal hydrogenation. The precursor tetraynes that undergo
Syntheses of trifluoroethylated unsymmetrical 1,3-diynes by using 1,1-dichloro-2,2,2-trifluoroethane
Zheng, Jian,Chen, Qing-Yun,Sun, Ke,Huang, Yangen,Guo, Yong
, p. 5757 - 5760 (2016/12/06)
Copper-mediated reaction of terminal 1,3-diynes with 1,1-dichloro-2,2,2-trifluoroethane (CF3CHCl2) using ethanolamine as ligand gave trifluoroethylated unsymmetrical 1,3-diynes in moderate to good yields. The reaction were carried out under mild conditions, and were easy to operate. Aryl groups with weak electron-withdrawing group or electron-donating group, and alkyl substitutents at terminal 1,3-diynes were tolerated. Synthesis of a trifluoroethylated conjugated triyne by using this method was demonstrated. Further transformation of the trifluoroethylated unsymmetrical 1,3-diyne to provide trifluoroethyl-substituted 1,2,3-triazole and isoxazole as application examples were successfully realized.
Highly enantioselective copper(i)-catalyzed conjugate addition of 1,3-diynes to α,β-unsaturated trifluoromethyl ketones
Sanz-Marco, Amparo,Blay, Gonzalo,Mu?oz, M. Carmen,Pedro, José R.
supporting information, p. 8958 - 8961 (2015/05/27)
The conjugate diynylation of α,β-unsaturated trifluoromethyl ketones is carried out in the presence of a low catalytic load (2.5 mol%) of a copper(i)-MeOBIPHEP complex, triethylamine and a terminal 1,3-diyne. Pre-metalation of the terminal 1,3-diyne with stoichiometric or higher amounts of dialkylzinc reagent is not required. The corresponding internal diynes bearing a propargylic stereogenic center are obtained with good yields and excellent enantioselectivities. This journal is
Copper-catalyzed three-component synthesis of 3-Aminopyrazoles and 4-iminopyrimidines via β-alkynyl-N-sulfonyl ketenimine intermediates
Xing, Yanpeng,Cheng, Binyu,Wang, Jing,Lu, Ping,Wang, Yanguang
supporting information, p. 4814 - 4817 (2015/04/27)
3-Aminopyrazoles and 4-iminopyrimidines were efficiently prepared via copper-catalyzed three-component reactions of butadiynes, sulfonylazides, and hydrazides or imidamides. The reactions were regioselectively approached via the formation of a β-alkynyl-N-sulfonyl ketenimine intermediate which represented a new and effective 1,3-dielectrophilic equivalent in organic synthesis.
Air-stable (phenylbuta-1,3-diynyl)palladium(II) complexes: Highly active initiators for living polymerization of isocyanides
Xue, Ya-Xin,Zhu, Yuan-Yuan,Gao, Long-Mei,He, Xiao-Yue,Liu, Na,Zhang, Wu-Yi,Yin, Jun,Ding, Yunsheng,Zhou, Hongping,Wu, Zong-Quan
, p. 4706 - 4713 (2014/04/17)
A family of air-stable (phenylbuta-1,3-diynyl)palladium(II) complexes were designed and prepared in a facile synthetic procedure. Their structures were characterized by 1H and 13C NMR, MS, and X-ray analysis. These Pd complexes were
Zinc-mediated enantioselective addition of terminal 1,3-diynes to N-arylimines of trifluoropyruvates
Zhang, Fa-Guang,Ma, Hai,Zheng, Yan,Ma, Jun-An
scheme or table, p. 7663 - 7669 (2012/09/05)
A facile and effective enantioselective addition of terminal 1,3-diynes to acyclic α-CF3 ketimine esters has been developed by using zinc/Binol complexes. The reaction works well with a variety of aromatic-, aliphatic- and silyl-substituted diynes, providing the desired products in up to 97% yield and 97% enantiomeric excess.
Mori-Hiyama versus hay coupling for higher polyynes
Gulia, Nurbey,Osowska, Karolina,Pigulski, Bartlomiej,Lis, Tadeusz,Galewski, Zbigniew,Szafert, Slawomir
experimental part, p. 4819 - 4830 (2012/10/18)
Dimerizations of C4 precursors RCa=CCa=CTMS [R = C 6H5 (1), p-CH3C6H5, (2), 4-n-C5H11C6H4 (3), C 6H9 (4), p-CH3O
